With parents who are UVA grads, Charlottesville has a lot of happy childhood memories for me. But I’ve loved this beautiful college town even more as an adult (maybe it’s all the vineyards?). If you’re looking for luxury, Keswick Hall is beautiful and The Clifton ranks in my top five stays ever, but neither are walking distance to town—and I think it’s a great town for exploring on foot. 

There’s no bad time to go to Charlottesville. Summer can be nice for the relative quiet without thousands of college kids, but I especially love fall—both for the energy around the university and for the crisp and colorful nearby mountainsides.  

Thursday

3 pm: On the drive into Charlottesville, stop at Pippin Hill Farm & Vineyards for cheese and wine on the patio.

5:30 pm: Arrive in Charlottesville, check in to Dinsmore Boutique Inn. (This convenient spot in downtown has the cutest unique rooms. I loved the Meriwether, and the Library Loft is very cool.)

7:30 pm: Walk down Main Street for dinner at Oakhart Social (reservations recommended, and don’t skip creative veggie sides like the roasted broccoli with fish sauce caramel).

Friday

8:30 am: Breakfast at Farm Bell Kitchen. (Purchase the inn package that includes breakfast at this charming street side restaurant on its ground floor. And be sure to order the crab beignets at least once.)

9:30 am: Depart for a hike at Humpback Rocks Loop, half an hour away (4.2-mile, moderately challenging trail with gorgeous views—especially during peak leaf season).

1 pm: Lunch at Blue Mountain Brewery (15-minute drive from trailhead with great patio views).

2:30 pm: Return to town to walk down Main Street and around the University of Virginia campus (be sure to stop at the new-ish Memorial to Enslaved Laborers).

6:30 pm: Dinner at Public Fish & Oyster House (reservations needed, remarkably good seafood for this far inland).

8:30 pm: Drinks at The Alley Light (cozy French vibe and amazing craft cocktails).

Saturday

9 am: Breakfast (again) at Farm Bell (Have you ordered the crab beignets yet?).

10 am: Driving service pick up for vineyard tours. (Unless you have a friend who wants to play DD.) There are so many great vineyards that it’s hard to pick, but I love going west of town to Stinson and King Family in Crozet (a polo match at King is still on my bucket list), followed by Veritas and Afton Mountain in Afton (have lunch with your tasting at Veritas, reservations recommended).

7 pm: Dinner on the Quirk rooftop (reservations recommended). 

Sunday

9:30 am: Coffee and pastries to-go from Farm Bell (unless you still haven’t tried the crab beignets).

10 am: Visit Monticello. Be sure to leave time to explore both the house and gardens. Or if you’re trying to work off some of the previous day’s wine and not especially interested in Thomas Jefferson, take a walk on the easy 4.3-mile Monticello Saunders Trail, which offers beautiful views of the Blue Ridge Mountains. 

12:30 pm: Lunch at Michie Tavern. Just a half mile down from Monticello, this is a historic tavern (ca. 1784) and it’s a period restaurant serving Southern fare (think fried chicken, black-eyed peas, mashed potatoes, lagers, and ales). It’s an experience everyone should do at least once. 

2 pm: Return home.